The Mid South 2026: In Good Company
On February 11th, 2026, I signed up for the Mid South for the second time.
Last year, my Mid South journey came to an end awkwardly at 6:00 AM outside of a gas station after commuting through darkness and unfamiliar roads, only to discover that while I was spending the evening with my family, preparing for the next morning, and getting all of the sleep that I needed, the Mid South was cancelled due to wildfires.
You see, I was entirely unaware of the situation in Stillwater because I was taking a sabbatical from social media. That is why I made the discovery, minutes away from the proposed starting line, at a gas station, while my wife was shuffling the kids to the bathroom.
This year, however, I knew that it would be different.
Not because I had the hope that the weather would cooperate, or because the weeks leading up to the Mid South seemed like they were leaning in our favor. I knew it was going to be different because I was ready.
Last year, the Mid South was going to be my first race. Historically, I have been a solo rider. I spent hours and hours alone on the bike, minding my business and experiencing the joy of being outside and using my body and mind to go from small town to small town until I would become officially lost. And last year, I was nervous. I was not prepared. And , to be honest, part of me was relieved when I found out that I would not be surrounded by hundreds of other people racing down gravel roads.
You see, I have struggled all of my life with imposter syndrome. In fact, so many paths I could have taken in life were flooded by my self-doubt and inability to seek guidance from others. My life as a musician failed. My life as a documentary filmmaker has seemingly come to an end. There were a lot of things that I held myself back from doing because I did not believe in myself.
And in 2025, the Mid South was going to be the ride that pushed me out of my comfort zone and into something that I so badly wanted to be a part of. But at the time, I was a little bit thankful that I found a way out of it.
And isn’t that sad?
Because of nerves and self-doubt, I was relieved that I did not have to step out of my shell and do something hard. However, little did I know that during the remainder of 2025, I was going to grow whether I liked it or not.
Shortly after this, I found out about Turkey Tuesday, a local group ride that happens at Turkey Mountain in Tulsa for mountain bikers. I had commented on a post asking if bringing a gravel bike would be okay. Overwhelmingly, people said yes. But there was one person who told me no.
His name is Bobby Reese, and he is not only well known in the cycling community, but has made a significant impact on our local trails, events, and races. He asked me to call him, and over the phone, he told me about Project Dudeman and a man named Brad Huff.
A day after my conversation with Bobby, I signed up for Project Dudeman because everything on the Tulsa Tough website rang true with the current phase of life I was in, my cycling journey, and my poor mental and spiritual health. And lucky for me, on April 19th, there was a Mental Fitness talk. But as per usual, I tried to find an excuse out of it.
Thankfully, my loving wife encouraged me to go, reminding me that I joined this group for a reason, which was saving our marriage and helping me rebuild myself as a husband, father, and as a man.
But my journey with Project Dudeman is a story for another day.
In short, after 11 months of riding with Project Dudeman, I was more prepared than ever for the Mid South 2026. So, like I said, on February 11th, I signed up and began planning my very, very short trip to Stillwater.
I arrived at Strickland Park at 1:00 PM on Thursday, in a borrowed Toyota 4Runner with a mattress and my Salsa Warbird in the back. Although I knew many friends from Tulsa would be there throughout the weekend, I had not made any plans to meet up with any of them. This is very unlike me.
Because for years, and even today, I have struggled with getting out of the house. And so I entered The Mid South nervous and anxious, but knowing deep down that I would fit in.
For the majority of the weekend, I wore a camera on my back. Each time that I rolled out on a shakeout ride, I wanted to capture as much as I could. The Mid South this year, for me, meant a lot more than roaring down gravel roads in the middle of nowhere. It showed me how much I had grown, how much I had matured, and how willing I have become to step outside of my shell and do uncomfortable things.
The morning of the ride was cold. I got dressed, prepared my bike, ate what I could, and made my way to the start. I was nervous, but not in the same way that I had been nervous the year before.
Without going too deep into the 50-mile ride, I will break it down this way.
It was very cold at the beginning.
My nerves vanished when I bombed down hills like a true hooligan.
I drank plenty of sugar and salt.
Climbing is my mortal enemy.
I recommend that you learn how to bunny hop.
Do not take yourself too seriously.
Stop at aid stations.
Be safe.
Have fun.
Enjoy yourself.
When I arrived at the finish line, I received the obligatory Bobby Wintle hug. My wife and kids celebrated with me. I ate a big burrito. And I recognized that I have grown a lot.
As a rider. As a father. And as a husband.
The Mid South was a dream come true. So, if you have been struggling and experiencing hard times, hop on your bike and ride the gravel roads around Stillwater, OK.
You’ll be in good company.